Publication Date:
2005
Short description:
Reductive lithiation of 1,3-dimethyl-2-arylimidazolidines / Azzena, Ugo Gavino; Giovanna, Dettori; Pisano, Luisa; Immacolata, Siotto. - In: TETRAHEDRON. - ISSN 0040-4020. - 61:13(2005), pp. 3177-3182.
abstract:
Naphthalene catalyzed lithiation of 1,3-dimethyl-2-phenylimidazolidine led to cleavage of the benzylic carbon–nitrogen bond,
with formation of an intermediate dianion. Under similar conditions, 1,3-dimethyl-2-(4-chlorophenyl)imidazolidine underwent
regioselective cleavage of the aromatic carbon–chlorine bond, leading to a 4-formylphenyllithium equivalent, whilst 1,3-dimethyl-2-(4-
methoxymethylphenyl)imidazolidine underwent regioselective cleavage of the benzylic carbon–oxygen bond, leading to a 4-formylbenzyllithium
equivalent.
with formation of an intermediate dianion. Under similar conditions, 1,3-dimethyl-2-(4-chlorophenyl)imidazolidine underwent
regioselective cleavage of the aromatic carbon–chlorine bond, leading to a 4-formylphenyllithium equivalent, whilst 1,3-dimethyl-2-(4-
methoxymethylphenyl)imidazolidine underwent regioselective cleavage of the benzylic carbon–oxygen bond, leading to a 4-formylbenzyllithium
equivalent.
Iris type:
1.1 Articolo in rivista
Keywords:
Aromatic aldehydes; Lithiation; Protective groups
List of contributors:
Azzena, Ugo Gavino; Giovanna, Dettori; Pisano, Luisa; Immacolata, Siotto
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